Estrogenic Activities of 517 Chemicals by Yeast Two-Hybrid Assay

doi:10.1248/JHS.46.282

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Journal Article•DOI•

Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals.

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Jianying Hu¹, Takako Aizawa•Institutions (1)

Peking University¹

01 Mar 2003-Water Research

TL;DR: A quantitative structure-activity relationship (QSAR) for structurally diverse phenols, nine alkylphenols with only oneAlkyl group, four hydroxyl biphenyls, bisphenol A and four natural and man-made estrogens was established by applying a quantum chemical modeling method.

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101 citations

Journal Article•DOI•

Formation of chlorinated derivatives of bisphenol A in waste paper recycling plants and their estrogenic activities

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Hitoshi Fukazawa, Masayuki Watanabe, Fujio Shiraishi, Hiroaki Shiraishi, Tatsushi Shiozawa¹, Hidetsuru Matsushita, Yoshiyasu Terao¹ - Show less +3 more•Institutions (1)

University of Shizuoka¹

01 Jun 2002-Journal of Health Science

TL;DR: The estrogenic activities of bisphenol A and its chlorinated derivatives were evaluated by an agonist assay using the yeast two-hybrid system with and without a metabolic activation test using rat liver S9.

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Abstract: High concentrations of bisphenol A were detected in the effluent from several pulping processes for waste paper containing thermal paper and/or other printed paper. Chlorinated derivatives of bisphenol A were found to be formed by its reaction with a low concentration of chlorine in the effluent from the bleaching process using sodium hypochlorite. Poly-chlorinated derivatives were mainly detected in the final effluents from two plants because they were not biodegraded in the water recycling process by treatment with activated sludge. The estrogenic activities of bisphenol A and its chlorinated derivatives were evaluated by an agonist assay using the yeast two-hybrid system with and without a metabolic activation test using rat liver S9. All of the chlorinated derivatives tested showed more potent activity than bisphenol A without S9. The activity of 3,3′-dichlorinated BPA was 38-fold stronger than that of bisphenol A. The activities of these compounds were almost eliminated upon treatment with S9.

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100 citations

Journal Article•DOI•

Acute toxicity, mutagenicity, and estrogenicity of biodegradation products of bisphenol-A.

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Michihiko Ike¹, Min-Yu Chen¹, Chang-Suk Jin², Masanori Fujita¹•Institutions (2)

Osaka University¹, Myongji University²

01 Jan 2002-Environmental Toxicology

TL;DR: It was concluded that biodegradation can remarkably reduce the toxic effects of BPA.

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Abstract: Biodegradation of bisphenol-A (BPA), which is known as an estrogenic chemical, proceeds via complicated metabolic routes and leads to formation of several kinds of biodegradation products. Through the major route BPA can be completely mineralized; however, p-hydroxyacetophenone (p-HAP), p-hydroxybenzaldehyde (p-HBAL), and p-hydroxybenzoic acid (p-HBA) are transiently accumulated at relatively high concentrations. On the other hand, degradation of BPA through the minor route tends to cause the accumulation of 2,3-bis(4-hydroxyphenyl)-1,2-propanediol and p-hydroxyphenacyl alcohol as the dead-end products. To fully assess the impact of BPA discharge into the environment, the considerable BPA degradation products p-HAP, p-HBAL, and p-HBA and the mixture of the dead-end products were examined for their acute toxicity, mutagenicity, and estrogenicity using the Daphtoxkit (Creasel Ltd.), umu test system, and yeast two-hybrid system, respectively. BPA was moderately toxic to Daphnia magna (48-h EC(50) was 10 mg/L) and weakly estrogenic, with activity that was 5 orders of magnitude lower than that of 17beta-estradiol in the yeast screen, though no mutagenicity was observed. All the tested BPA biodegradation products showed very low acute toxicity compared with BPA, and none was mutagenic. A slight estrogenic activity was detected only for p-HAP among the tested degradation products. It was concluded that biodegradation can remarkably reduce the toxic effects of BPA.

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100 citations

Journal Article•DOI•

Endocrine disruptors induce cytochrome P450 by affecting transcriptional regulation via pregnane X receptor

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Eriko Mikamo¹, Shingo Harada¹, Jun-ichi Nishikawa¹, Tsutomu Nishihara¹•Institutions (1)

Osaka University¹

15 Nov 2003-Toxicology and Applied Pharmacology

TL;DR: Findings suggest that some EDs affect sex hormone receptor indirectly by induction of metabolic enzyme via PXR, to produce rapidly higher concentrations of effective metabolites, leading to disturbance of the endocrine system.

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99 citations

Cites background from "Estrogenic Activities of 517 Chemic..."

...Some chemicals or their metabolites bind to sex steroid hormone receptors (androgen receptor (AR) and estrogen receptor (ER)) directly and influence the expression of target genes (Nishihara et al., 2000; Blair et al., 2000; Yoshihara et al., 2001; Sultan et al., 2001)....
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Journal Article•DOI•

Disruption of endocrine function in in vitro H295R cell-based and in in vivo assay in zebrafish by 2,4-dichlorophenol

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Yanbo Ma¹, Jian Han¹, Yongyong Guo¹, Paul K.S. Lam², Rudolf S.S. Wu³, John P. Giesy, Xiaowei Zhang⁴, Bingsheng Zhou¹ - Show less +4 more•Institutions (4)

Chinese Academy of Sciences¹, City University of Hong Kong², University of Hong Kong³, Nanjing University⁴

15 Jan 2012-Aquatic Toxicology

TL;DR: It is demonstrated that 2,4-DCP modulates transcription of steroidogenetic genes in both H295R cells and in the zebrafish HPG-axis and disrupts steroidogenesis, which in turn, can cause adverse effects on reproduction in fish.

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98 citations

Cites background from "Estrogenic Activities of 517 Chemic..."

...For example, by use of a yeast 1 ology t o g ( a h ( t t i t r d E e a s p s a b t 2 b ( i m s c ( e c p c p o f t p p ( 2 a d p i l ( e o r d o 2 s o h s i 1 o l ( 74 Y. Ma et al. / Aquatic Toxic wo-hybrid transactivation reporter gene assay, 2,4-DCP was bserved to cause effects mediated through the ERE (estroen responsive element) in a concentration-dependent manner Nishihara et al., 2000)....
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...…( e c p c p o f t p p ( 2 a d p i l ( e o r d o 2 s o h s i 1 o l ( 74 Y. Ma et al. / Aquatic Toxic wo-hybrid transactivation reporter gene assay, 2,4-DCP was bserved to cause effects mediated through the ERE (estroen responsive element) in a concentration-dependent manner Nishihara et al., 2000)....
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...In a yeast two-hybrid assay, 2,4-DCP has been shown to be estrogenic by initiating the binding of ER and ER responsive element (ERE) (Nishihara et al., 2000), and promote proliferation of cells in human breast tumor cells (MCF-7) (Jones et al....
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...In a yeast two-hybrid assay, 2,4-DCP has been shown to be estrogenic by initiating the binding of ER and ER responsive element (ERE) (Nishihara et al., 2000), and promote proliferation of cells in human breast tumor cells (MCF-7) (Jones et al., 1998)....
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Book•

Our Stolen Future

[...]

Theo Colborn, Dianne Dumanoski, John Peterson Myers

01 Jan 1996

TL;DR: The cause of disruptions in animal breeding cycles, accompanied by increases in birth defects, sexual abnormalities and reproductive failure, is traced to the pervasive presence in the environment of chemicals that mimic hormones and trick the reproductive system.

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Abstract: For years, scientists have noticed disruptions in animal breeding cycles, accompanied by increases in birth defects, sexual abnormalities and reproductive failure. Humans are not immune either, with sperm counts dropping by as much as 50% in recent decades and with women seeing a rise in hormone-related cancers, endometriosis and other disorders. This book traces the cause of these aberrations and diseases to the pervasive presence in the environment of chemicals that mimic hormones and trick the reproductive system. The conclusions are as obvious as they are inescapable - unless we make vital changes in the way we manufacture and employ the artefacts of our "good life", there will be no life at all.

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917 citations

Estrogenic Activities of 517 Chemicals by Yeast Two-Hybrid Assay

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Cites background from "Estrogenic Activities of 517 Chemic..."

Cites background from "Estrogenic Activities of 517 Chemic..."

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